74568-06-2

Usage

Uses

Used in Chemical Analysis Industry:
(R)-4-UNDECANOLIDE STANDARD FOR GC is used as a reference standard for calibrating gas chromatography instruments. It provides a consistent and known reference for comparison, which is essential for the accurate measurement and identification of various compounds in samples.
Used in Research and Development:
(R)-4-UNDECANOLIDE STANDARD FOR GC is used as a tool in research and development for the identification and quantification of unknown compounds in samples. It helps scientists and researchers to validate their findings and improve the reliability of their results in various chemical and material research fields.

Upstream product

• 139126-66-2 4-Hydroxy-undecanoic acid propyl ester 
• 82854-54-4 (9Z,13E)-12-hydroxy-9,13-octadecadienoic acid 
• 107736-71-0 (R)-4-Hydroxy-undecanoic acid ethyl ester 
• 107736-61-8 (R)-4-Acetoxy-undecanoic acid ethyl ester 
• 104-67-6 5-heptyldihydro-2(3H)-furanone 
• 90199-73-8 4-oxooct-7-enoic acid 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 21369-64-2 n-hexyllithium 
• 85428-31-5 3-(S)-oxiranyl-propionic acid methyl ester 
• 56-86-0 L-glutamic acid 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 1233882-68-2 C₂₅H₃₂N₂O₅ 
• 1233882-53-5 C₂₀H₃₁NO₃ 

Downstream Products

• 74568-05-1 (4S)-4-heptyl-γ-butanolide 

Relevant academic research and scientific papers

Synthesis method of gamma-or delta-substituted alkyl chiral lactone

The invention discloses a synthesis method of gamma-or delta-substituted alkyl chiral lactone, the synthesis method comprises the following steps: mixing nickel salt, a chiral bidentate organic phosphorus ligand, aliphatic gamma-or delta-ketonic acid and a solvent, and carrying out asymmetric reduction reaction under the action of a reducing agent to obtain the gamma-or delta-substituted alkyl chiral lactone. According to the invention, asymmetric hydrogenation of aliphatic gamma-and delta-ketonic acids is realized through a cheap, green and efficient homogeneous chiral nickel-phosphorus complex catalytic system, and gamma-or delta-substituted alkyl chiral lactone is obtained with excellent yield and high enantioselectivity.

Stereoselective synthesis of chiral δ-lactonesviaan engineered carbonyl reductase

A carbonyl reductase variant,SmCRM5, fromSerratia marcescenswas obtained through structure-guided directed evolution. The variant showed improved specific activity (U mg?1) towards most of the 16 tested substrates and gave high stereoselectivities of up to 99% in the asymmetric synthesis of 13 γ-/δ-lactones. In particular, SmCRM5showed a 13.8-fold higher specific activity towards the model substrate,i.e., 5-oxodecanoic acid, and gave (R)-δ-decalactone in 99% ee with a space-time yield (STY) of 301 g L?1d?1. The preparative synthesis of six δ-lactones in high yields and with high enantiopurities showed the feasibility of the biocatalytic synthesis of these high-value-added chemicals, providing a cost-effective and green alternative to noble-metal catalysis.

Carboxyl Group-Directed Iridium-Catalyzed Enantioselective Hydrogenation of Aliphatic ?-Ketoacids

Although the transition metal-catalyzed asymmetric hydrogenation of aromatic ketones has been extensively explored, the enantioselective hydrogenation of aliphatic ketones remains a challenge because chiral catalysts cannot readily discriminate between the re and si faces of these ketones. Herein, we report a carboxyl-directing strategy for the asymmetric hydrogenation of aliphatic ?-ketoacids. With catalysis by iridium complexes bearing chiral spiro phosphino-oxazoline ligands, hydrogenation of aliphatic ?-ketoacids afforded chiral ?-hydroxylacids with high enantioselectivity (up to 99% ee). Mechanistic studies revealed that the carboxyl group of the substrate directs hydrogen transfer and ensures high enantioselectivity. Density functional theory calculations suggested the occurrence of chiral induction involving a hydrogen-hydrogen interaction between a hydride on the iridium atom and the substituent on the oxazoline ring of the ligand, and on the basis of the calculations, we proposed a catalytic cycle involving only Ir(III), which differs from the Ir(III)/Ir(V) catalytic cycle that operates in the hydrogenation of α,β-unsaturated carboxylic acids.

Efficient Stereoselective Synthesis of Structurally Diverse γ- and δ-Lactones Using an Engineered Carbonyl Reductase

Structurally diverse γ- and δ-lactones were efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500-fold) and thermostability toward 14 γ-/δ-keto acids and esters, compared with the wild-type enzyme, with 110-fold enhancement in catalytic efficiency (kcat/Km) toward methyl 4-oxodecanoate. The preparative synthesis of alkyl and aromatic γ- and δ-lactones with 95 %–>99 % ee and 78 %–90 % yields was demonstrated. The highest space-time yield, 1175 g L?1 d?1, was achieved for (R)-γ-decalactone.

Stereochemical elucidation of streptorubin B

Streptorubin B is a structurally remarkable mem-ber of the prodiginine group of antibiotics produced by several actinobacteria, including the model organism Streptomyces coelicolor A3(2). Transannular strain within the pyrrolophane structure of this molecule causes restricted rotation that gives rise to the possibility of (diastereomeric) atropisomers. Neither the relative nor the absolute stereochemistry of streptorubin B is known. NOESY NMR experiments were used to define the relative stereochemistry of the major atropisomer of streptorubin BHCl in solution as anti. We exploited this finding together with our knowledge of streptorubin B biosynthesis in S. coelicolor to determine the absolute stereochemistry of the anti atropisomer. 2-Undecylpyrrole stereoselectively labeled with deuterium at C-4′ was synthesized and fed to a mutant of S. coelicolor, which was unable to produce streptorubin B because it was blocked in 2-undecylpyrrole biosynthesis, and in which the genes responsible for the last two steps of streptorubin B biosynthesis were overexpressed. 1H and 2H NMR analysis of the stereoselectively deuterium-labeled streptorubin BHCl produced by this mutasynthesis strategy allowed us to assign the absolute stereochemistry of the major (anti) atropisomer as 7′S. HPLC analyses of streptorubin B isolated from S. coelicolor on a homochiral stationary phase and comparisons with streptorubin B derived from an enantioselective synthesis showed that the natural product consists of an approximately 88:7:5 mixture of the (7′S, anti), (7′S, syn), and (7′R, anti) stereoisomers.

Combination of novozym 435-catalyzed hydrolysis and mitsunobu reaction for production of (r)γ-lactones

Chiral-lactones of both enantiomers were synthesized with more than 90% optical purities. The key step was Novozym 435-catalyzed hydrolysis of racemic N-benzyl-4-acetoxyalkylamides. Additionally, because (R)-γ-lactones are predominant in apricot, mango, peach, passion fruit, and strawberry, synthesis was attempted using only one enantiomer selectively. The (R)-enantimer was synthesized with more than 80% total yield and more than 90% optical purity by a combination of Novozym 435-catalyzed hydrolysis and the Mitsunobu reaction. Copyright

Gamma-Undecenolactone, Method for the Preparation and Use Thereof for Cosmetics and in the Form of Food Additives

The invention relates to a gamma-undecenolactone of formula (I), wherein a lactonic cycle can carry an unsaturation between carbon No2 and carbon No3 and is preferably saturated, RI is a possibly substituted C7 alkenyl or alkynyl group comprising at least one unsaturation, and preferably RI is an CH2═CH—CH2—CH2—CH2—CH2—CH2 group, said gamma-undecenolactone contains an asymmetric carbon in position 4 having (R) or (S) configuration. The biosynthesis of said gamma-undecenolactone and the use thereon for perfumery and for a food flavouring agent are also disclosed.

Stereoselective allylation of aldehydes on solid support and its application in biology-oriented synthesis (BIOS)

A systematic study on the asymmetric allylation of aldehydes on solid support is reported. Different kinds of chiral allylboron reagents with complementary direction of stereoinduction were applied successfully in this reagent-controlled transformation. T

Facile synthesis of optically active γ-lactones via lipase-catalyzed reaction of 4-substituted 4-hydroxybutyramides

Lipase-catalyzed transesterification of racemic 4-substituted 4- hydroxybutyramides with succinic anhydride proceeded enantioselectively to afford (S)-succinic acid monoester and unreacted (R)-4-hydroxybutyramide derivative, which were separated easily by

STEREOCHEMISTRY OF THE BIOGENERATION OF γ-DECANOLIDE

Microbial degradation of the racemic unsaturated hydroxy acids, 1, 2 and 3, and of racemic γ-decanolide affords (R)- and (S)-γ-decanolide of variable ee values, depending upon the microorganism.